1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩
1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩 · 1-エチル-3-[3-(ジメチルアミノ)プロピル]カルボジイミド·塩酸 · 3-(3-ジメチルアミノプロピル)-1-エチルカルボジイミド·塩酸塩 · N-[3-(ジメチルアミノ)プロピル]-N'-エチルカルボジイミド·塩酸塩 · 1-[3-(ジメチルアミノ)プロピル]-3-エチルカルボジイミド·塩酸 · 1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド·塩酸塩 · 1-[3-(ジメチルアミノ)プロピル]-3-エチルカルボジイミド·塩酸塩 · N'-(3-ジメチルアミノプロピル)-N-エチルカルボジイミド·塩酸塩
識別子と物理属性
| CAS No. | 25952-53-8 |
|---|---|
| 分子式 | C8H18ClN3 |
| 平均分子量 | 191.7 g/mol |
| 単同位体質量 | 191.1189253 g/mol |
| SMILES | CCN=C=NCCCN(C)C.Cl |
| InChIKey | FPQQSJJWHUJYPU-UHFFFAOYSA-N |
| PubChem CID | 2723939 |
| ChEMBL | CHEMBL1968770 |
| EC No. | 247-361-2 |
| DTXSID | DTXSID50880076 |
| 現地名 | 1-エチル-3-(3-ジメチルアミノプロピル)カルボジイミド塩酸塩 |
化学・物理的性質
| 極性表面積 | 28 |
|---|---|
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 5 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 134 |
| Physical Description | White powder[Aldrich MSDS] |
| 融点 | 110-115 °C(lit.) |
| 密度 | 0.877 g/mL at 20 °C(lit.) |
| 蒸気圧 | 0.002Pa at 20℃ |
| 屈折率 | n20/D 1.461 |
| 貯蔵条件 | -20°C |
| 溶解度 | H2O: 溶解度 1gm/10ml、透明～ごくわずかに濁り、無色～ごくわずかに黄色溶ける |
| 外観・状態 | 結晶性粉末 |
| 色 | ホワイトからオフホワイト |
| BRN | 5764110 |
| 安定性 | 安定していますが、湿気に弱いです。強酸、強力な酸化剤、湿気とは相容れない。 |
| 主な用途 | 微生物学 |
| InChI | 1S/C8H17N3.ClH/c1-4-9-8-10-6-5-7-11(2)3/h4-7H2,1-3H31H |
| InChIKey | FPQQSJJWHUJYPU-UHFFFAOYSA-N |
| SMILES | Cl.CCN=C=NCCCN(C)C |
| LogP（分配係数） | -2.98 at 25℃ |
| CAS データベース | 25952-53-8(CAS DataBase Reference) |
| EPAの化学物質情報 | 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride (25952-53-8) |
化学的特性
EDC-HCl, or 1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, is a white crystalline powder that easily deliquescent and can dissolve in both water and ethanol. It is commonly used as an activating reagent in amide synthesis to activate carboxyl groups. It can also activate phosphate groups, cross-link proteins and nucleic acids, and produce immunocouplers. EDC-HCl is commonly applied in the pH range of 4.0-6.0 and is often used in conjunction with N-Hydroxysuccinimide (NHS) or N-Hydroxysulfosuccinimide sodium salt to improve coupling efficiency.
安全性と法規制
| GHS 分類 | DangerH302 (73.7%): Harmful if swallowed [Warning Acute toxicity, oral]H311 (56.5%): Toxic in contact with skin [Danger Acute toxicity, dermal]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (60.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (10.2%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (75.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H335 (43.2%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H373 (55.9%): May causes damage to organs through prolonged or repeated exposure [Warning Specific target organ toxicity, repeated exposure]H400 (56.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (56.5%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P260, P261, P262, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 315 reports by companies from 35 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: 1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideStatus: Active Update: 08-06-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/23229Status: Active Update: 28-04-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/17871N-(3-Dimethylaminopropyl)-N'-ethylcarbodiimide hydro chloride: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | A skin and strong eye irritantMay cause allergic reactions in certain individuals[Aldrich MSDS] |
| Hazard Classes and Categories | Acute Tox. 4 (73.7%)Acute Tox. 3 (56.5%)Skin Irrit. 2 (100%)Skin Sens. 1 (60.6%)Eye Dam. 1 (10.2%)Eye Irrit. 2 (75.2%)STOT SE 3 (43.2%)STOT RE 2 (55.9%)Aquatic Acute 1 (56.2%)Aquatic Chronic 1 (56.5%) |
| F | 1-3-10 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | FF2200000 |
| 輸送番号（UN） | UN 2735 8/PG 3 |
| 毒性 | LD50 intravenous in mouse: 56mg/kg |
| 税関コード | 29252000 |
| 危険文句（R） | 34-36/37/38-41-37/38-20/21/22 |
| 化審法 | (2)-1696 |
| 危険表示 | C,Xi |
| hazard_note | Irritant |
| 安全措置（S） | 26-36/37/39-45-37/39-36 |
| 危険等級 | Acute Tox. 3 DermalAcute Tox. 4 OralAquatic Acute 1Aquatic Chronic 1Skin Irrit. 2Skin Sens. 1STOT RE 2 Oral |
| 貯蔵分類 | 6.1C - Combustible acute toxic Cat.3toxic compounds or compounds which causing chronic effects |
用途
用途
有機合成化学において、カルボジイミド基を含む化合物は脱水縮合剤として用いられる。良く使われる例としてはカルボン酸に対するアミド結合、もしくはエステル結合形成の促進である。脱水縮合を促進させ、かつ副反応を抑制するための添加剤として 1-ヒドロキシベンゾトリアゾール (HOBt) や N-ヒドロキシコハク酸イミド (HOSu) などが良く用いられる。
用途
ペプチド合成用。
一般的な説明
EDC hydrochloride is a water-soluble derivative of carbodiimide useful for conjugating haptens to proteins and polypeptides. Used to modify NMDA receptors and as a condensing agent in peptide synthesis. The major advantage of EDAC coupling is the easy removal of excess reagent and the corresponding urea by washing with dilute acid or water. Carbodiimides catalyze the formation of amide bonds, carboxylic acids, and amines by activating the carboxylate to form an O-acylurea. This intermediate can be attacked by an amine directly to form an amide. EDAC is released as a soluble urea derivative.
製法・合成法
純化方法
It is an excellent H2O-soluble peptide coupling reagent. It is purified by dissolving (ca 1g) in CH2Cl2 (10mL) at room temperature and then add dry Et2O (~110mL) dropwise and the crystals that separate are collected, washed with dry Et2O, recrystallised from CH2Cl2/Et2O and dried in a vacuum over P2O5. It is important to work in a dry atmosphere or work rapidly and then dry the solid as soon as possible. The material is moderately hygroscopic, but once it becomes wet it reacts slowly with H2O. Store it away from moisture at -20o to slow down the hydrolysis process. The free base has b 47-48o/0.27mm, 53-54o/0.6mm, n 1.4582. The methiodide is recrystallised from CHCl3/EtOAc, the crystals are filtered off, washed with dry Et2O, recrystallised from CHCl3/Et2O, and dried in vacuo over P2O5, m 93-95o, 94-95o. [Sheehan et al. J Am Chem Soc 87 2492 1965, Sheehan & Cruickshank Org Synth Coll Vol V 555 1973.] § A polymer bound version is commercially available.